


Cherry Impala

by WinJennster



Category: Supernatural
Genre: Dean Winchester Has a Panty Kink, Drag Queen Dean Winchester, M/M, Panties, Pretty Dean Winchester, Supportive Castiel (Supernatural)
Language: English
Status: Completed
Published: 2019-08-09
Updated: 2019-08-09
Packaged: 2020-08-13 11:57:48
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,106
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20173876
Author URL: https://archiveofourown.org/users/WinJennster/pseuds/WinJennster
Summary: Rhonda Hurley. To nineteen year old Dean, she seemed a goddess. Dean didn’t know what type of bar he’d stumbled into at the time, but man--all the women in the place were tall, big, statuesque. Flawlessly made up faces, gorgeous outfits, shining like diamonds. Dean was smitten with all of them immediately.In which Drag Queen Cherry Impala remembers what it took to get her to where she is now.





	Cherry Impala

When Dean Winchester was nineteen years old, getting laid was pretty much the only thing on his mind. That, and sneaking into bars that he legally wouldn’t be able to get into for two more years. 

Years of being on the road with his dad made it easy. He was always the mysterious new boy in town, and all he had to do was flutter his ridiculously long lashes at them, maybe buy them a drink, and he’d find himself deep in some pretty girl’s body before the night ended. 

But one Friday night in New York City changed the entire course of his life--and looking back, Dean was damn glad it had. Dad and Sammy otherwise occupied, Dean rode the subway into Manhattan and found a bar that looked like a sure bet.

Fiddling with his iPod, he finds the song he’s looking for, smiling as the first notes played over his sound system. Dean settles at his vanity and grins at the clean shaven face staring back. 

Rhonda Hurley. To nineteen year old Dean, she seemed a goddess. Dean didn’t know what type of bar he’d stumbled into at the time, but man--all the women in the place were tall, big, statuesque. Flawlessly made up faces, gorgeous outfits, shining like diamonds. Dean was smitten with all of them immediately. 

Thinking back on those days, Dean mouths the words along with George Michael as he slides his wig cap into place, making sure all his short, cropped hair is trapped inside. He opens a glue stick and smears it over his eyebrows, using a brush to flatten them down. 

Rhonda had bought him a drink that night, perched on the stool next to him. She had neon pink hair in huge curls that perfectly matched the pink of her full, thick lips. When she asked, he said a beer, but she ordered him a cosmo instead. 

Dean regards his face critically. He wishes he had the balls to shave his eyebrows off completely, but some part of him won’t allow it. Not that it would matter. He does this everyday, and filling in missing eyebrows is normal now. Still--

He reaches for the first palette and starts contouring his forehead. Dean is meticulous as he applies his foundation, taking care not to let it cake in his crow’s feet. He highlights his cheekbones, smiling as he see her start to come through, that beautiful woman that lives inside of ordinary Dean Winchester. 

There was a beautiful woman that lived inside of a man named Malcolm Johnson, too. Dean knew her as Rhonda. And in one night, she taught him more about himself than he’d ever hoped to learn. Back in her apartment, she revealed the truth under her clothes and Dean was unalarmed. He was smitten, crazy about her. 

“Baby, you got someone beautiful inside you, too,” she’d purred as she dressed him in her panties. 

Dean hadn’t been able to tear his eyes away from the hot pink satin clinging to his hips and ass. Rhonda sat Dean at her vanity. He stayed still as she lined his eyes, plucked his brows and did up his lips. She put a wig cap on him and a long, pink wig. False eyelashes followed, then she laced him into a corset the same color as the panties. 

In all his life, Dean had never felt so gorgeous. 

Rhonda put on _ Freedom ‘90 _ and fucked him from behind while he watched himself in the mirror. In the afterglow, she held him in her strong arms and told him not to be afraid of the beauty inside him. 

Dean smooths powder over his skin, setting the foundation. Eyebrows are drawn in, and his brow bone highlighted. Opening his brand new Jeffree Starr Jawbreaker palette, he starts working on his eye look--deep reds highlighted with pink and lined dramatically in deep, dark black. 

Sam went away to college eventually, and Dean left his alcoholic father after John kicked his ass for giving a blowie in the back seat of the Impala. It was no loss, really. Rhonda welcomed him back to NYC and introduced him to new and wonderful friends. One of them--

“Does this look ok?” Dean smiled at the voice and turned to see his husband struggling with his tie. “I bought this one to match your dress. Is it ok?”

Dean stood and crossed the dressing room to take it from Cas’s hands. “It’s perfect, baby.” Lifting Cas’s shirt collar, Dean runs the red silk around Cas’s neck, tying it deftly before smoothing his collar back down. “Fuck, you’re gorgeous. No one will be looking at me tonight.”

“I highly doubt that. They’re coming to see you, after all. Cherry Impala, Queen of the Queens.”

“Flatterer,” Dean smiles, cheeks warming. Fuck, that never got old. He leans forward and kisses Cas’s cheek. “I need to finish getting ready.”

“Of course, darling. I’ll leave you to your makeup and Mr. Michael.” 

“Thanks, babe. I’ll need your help with the corset.”

“Your wish is my command, Miss Impala.” 

Dean chuckles as Cas leaves the dressing room. Sitting back down, Dean finishes his makeup with inch long false eyelashes and fire engine red lips. He tops it all off with a generous dusting of microfine glitter. 

Rhonda told Dean, on his return to New York, that a boy that looked like him would make a killing as a drag queen. No one could have ever predicted it would make him rich and famous. 

Massive red wig firmly in place, Dean calls for Cas, and watches in the mirror as his gorgeous husband, stunning in his perfectly fitted Dior tuxedo, carefully laces Dean into his corset. He helps Dean with his stockings and garter belt, smoothing his hands over Dean’s silk covered ass. He waits patiently as Dean dons red satin opera gloves, red platform heels, all of his red rhinestone jewelry, and a last touch of lipstick. Cas helps Dean pin his crown in his hair, and then helps him into a red sequined dress. 

Dean never dreamed drag would take him so far and so high, and he sure as hell never dreamed that it would net him the man of his dreams, a man that is happily helping him into his faux fur coat. 

They arrive at the club to preside over the crowning of Miss Drag New York 2019, and there’s much cheering and applause as Dean--as Miss Cherry Impala enters the room on her husband’s arm. She meets Rhonda’s eyes from across the crowd and smiles. 

It’s good to be Queen. 

  
  
  



End file.
